Synlett 1991; 1991(10): 712-714
DOI: 10.1055/s-1991-34771
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A New Approach to the Synthesis of 2-Aza-1,3-Dienes through a Novel 1,4-Rearrangement of a Trimethylsilyl Group from Nitrogen to Carbon

A. Degl'lnnocenti* , A. Mordini, D. Pinzani, G. Reginato, A. Ricci
  • *Centro CNR Composti Eterociclici c / o Dipartimento di Chimica Organica "U. Schiff". via G. Capponi 9,I-50121 Firenze, Italy
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
13. März 2002 (online)

The metalation of N,N,3-tris(trimethylsilyl)-2-propen-1-amine (1) with the equimolar mixture butyllithium/diisopropylamine/potassium tert-butoxide, followed by quenching with aldehydes or ketones, leads to substituted 2-aza-1,3- dienes (N-alkylidene-3,3-bis(trimethylsilyl)-1-propen-1-amines) in satisfactory yield through a novel N → C 1,4-rearrangement of a trimethylsilyl group.